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Electrochemical Synthesis of Isoxazolines: Method and Mechanism

submitted on 22.12.2020, 23:07 and posted on 24.12.2020, 04:55 by Samuel David Lee Holman, Neal Fazakerley, Darren poole, Diane M. Coe, Leonard Berlouis, Marc Reid
An electrochemical method for the green and practical synthesis of a broad range of substituted isoxazoline cores is presented. Both aryl and more challenging alkyl aldoximes are converted to the desired isoxazoline via an electrochemically enabled regio- and diastereoselective reaction with electron-deficient alkenes. Additionally, in-situ reaction monitoring methods compatible with electrochemistry equipment have also been developed in order to probe the reaction pathway. Supporting analyses from kinetic (time-course) modeling and density functional theory support a stepwise, radical-mediated mechanism, and discounts hypothesized involvement of closed shell [3+2] cycloaddition pathways.


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University of Strathclyde


United Kingdom

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No conflict of interest.